Course Correction
FOR MUCH OF MY LIFE, I only had to deal with financial issues in the abstract, the result of being born into an economically comfortable family that worried little about spending choices. But like all good privilege stories, I had my comeuppance and resurrection.
I grew up with just about every privilege a person could want. My family was as stereotypical a nuclear, suburban, well-to-do group as any seen on a TV sitcom. I never wanted for food, shelter, top-flight schooling or the latest comforts. I was born wealthy, male and white in America. The road to success was flat and freshly paved.
Budgets, paying bills and other pragmatic aspects of finance were discussed in our family. But I kept all this knowledge at arm's length. Money was, for me, a valued but undefined resource that didn���t necessarily need management, like living in a forest and never worrying about running out of timber.
My father was self-made. He had taken a money-losing curtain, drapery and bedspread company and turned it into the country���s leading producer of such goods. He was hands-on with everything, overseeing all the manufacturing plants and making personal sales trips to JC Penney in New York and Walmart in Arkansas.
He was also pragmatic. I remember excitedly showing him one of my comic books that was, according to a collector���s guide, worth $50. My father smiled and asked, ���Do you know anyone right now who will pay you $50 for that comic?��� When I sheepishly said no, he put his arm on my shoulder and said, ���Then it���s not worth $50.���
If Pop had a fault, it was that he was too generous with his kids. He wanted us to be free of money worries so we could pursue our dreams. But there was a cost. While I learned to stay mostly within my allowance and spend reasonably, there was no harsh penalty for blowing the budget once in a while. I learned about stocks and watched interest rates���I grew up during the inflationary 1970s���but I also knew I had a safety net if I made a bad choice. My privilege told me that money took care of itself. I needn���t worry about paying for college and law school, so I didn���t.
One good lesson I learned from watching my father���though it didn���t immediately stick���was that just because we could afford the best didn���t mean we should spend that much. If a salesman tried to talk my father into buying the high-end deluxe model, my father would point-blank ask, ���Tell me what exactly makes this version worth so much more than the other one, and then I���ll judge.��� We learned that the basic version of things, like a car, was almost always enough.
I came out of law school ready to take on the world and, with a good job in hand, I again didn���t need to worry about money. I had plenty to live on and even invest. I bought stocks and municipal bonds. I won���t say I bought wisely. It was pretty much hunches supported by a little research. Despite being mid-20s and having spent almost all my life in school, I thought of myself as an advanced investor because I was using the latest high tech, in the form of a 640 KB RAM personal computer, as well as programs like Quicken, to monitor it all. In truth, I was like a novice driver in a Ferrari.
When spending, I resisted buying big-ticket items, except, of course, those that I ���needed,��� like expensive designer suits to play power litigator in court. Where I was most undisciplined was day-to-day expenses. I usually ate at good restaurants. If I needed something, I opted for convenience, rather than spending time shopping for a better deal. Also, at this point, in my haughty 20-something-knows-everything mind, I opted to counter my father���s example and buy more expensive versions of everything from tires to furniture to wine. That way, in my na��ve thinking, I knew I was getting quality.
I married another lawyer and we moved to Dallas, each working for a different law firm. We bought a starter home and began a family with the birth of our son. We each saved and invested, but we kept our investments mostly separate, except for shared things like the mortgage.
My rude awakening. For the U.S., the 1990s was a time of strong growth. For me, it was my crash. I came to realize what I had felt intuitively for a long time: I hated being a lawyer. It was what society said was ���success,��� but it wasn���t for me. I was raised with a sense of noblesse oblige, that my privilege not only allowed��me to give back to society, but that I had a duty to do so. As a business litigation attorney, I was giving little back, instead simply moving piles of money from one rich party to another, while also keeping a chunk for the law firm. I hated the monotonous day-to-day grind. It showed in my work and attitude. I was paid well, but I put on weight and had chest pains.
I quit law. Lawyers don���t have a lot of transferable skills���that���s why they���re usually the first chosen to be eaten in surveys of people told to imagine they were marooned. I looked around for what I could do to both serve humanity and still serve my son food. I found it in teaching. I put together a resume and sent off letters to schools, saying I was a lawyer who wanted to teach and please give me a shot. I substitute-taught to see if I liked it and could handle being in a classroom. I loved it.
During this time, I had a long lunch with my father, discussing my career transition. He just wanted me to be happy. For my part, I told him I owed him an apology. Growing up among elite kids, I was somewhat embarrassed that my father was so bourgeois as to make money by manufacturing curtains and bedspreads. I now realized that he made a tangible product that improved people���s lives and, in the process, he and Mom created a wonderful environment for their kids to grow up in. I���m glad I got to say this before his passing.
At around the same time, my marriage fell apart. My now ex-wife and I were friends who had the law in common, but we weren���t good as a couple. For one, I had already lived with privilege, and didn���t really desire club memberships and the latest doo-dads. Been there, done that. My ex had grown up modestly in a rural town where young girls were told the best they could do was marry the local seed salesman. Law and the lawyer lifestyle were her vehicles to self-reliance and to prove her worth.
Neither of us was right or wrong, but we had different aspirations. Now that I wasn���t a lawyer and could no longer afford to spend without thought, the marriage crumbled. She retained primary custody of our son, so she got the lion���s share of our assets. I put most of the assets I had to give her into a college fund for our son.
Luckily, I proved good at teaching and managed to get a great job and remain employed for the rest of my career. The problem: I was pretty much starting over. My savings were gone in the divorce. I had the spending habits of a lawyer, but a teacher���s salary. I was forced to limit how often I ate out and care whether something was on sale. I had one fancy leftover bit of bling, a shiny red convertible with a $450 monthly lease payment. I broke the lease, paid a large penalty and bought a plain PT Cruiser. My toddler son was disappointed that we could no longer jump in and out of the convertible, but he loved the Chrysler emblem on the Cruiser because it looked like Harry Potter���s golden snitch. It was a reminder that it isn���t things that bring meaning to our lives. Rather, it���s the meaning and appreciation we invest in them.
I tried to live within a budget, but having never done so, it took a long time to corral my spending. Still, I maxed out my contributions to my 403(b) plan. Our school���s retirement services manager, TIAA-CREF, made it easy to do basic research and pick funds. I was finally able to join the rest of the country���s rising 1990s portfolios by buying global funds, tech shares and some adventurous gambles on small-cap funds.
Even as I invested, though, the credit card was my best friend and worst enemy. I had, of course, endless offers for new cards, with assurances I only had to pay the minimum each month. I never bought big, but the ���what the heck��� instances were like body blows to my credit score.
I had two weaknesses. First, I tried to keep up with my ex. If she took my son on a great vacation or bought him tons of gifts, I feared he would prefer her, so I acted like a third-world economy trying to keep pace with a first-world one. Eventually, I had to look for shortcuts and freebies. Instead of vacations, we did ���buddy hikes��� and made secret buddy caves in the woods. We saved cardboard, and built forts and other things.
My other big money leak was dating. I was fixed up with lawyers, businesswomen and other professionals. The expectation was to ���do the town.��� Flowing cash would supposedly make the evening flow better. I was even told by a dating consultant to lie and say I was still a lawyer because ���no woman wants to date a teacher.���
Ironically, while I was watching my debt rise, I began teaching economics and started seeing a disconnect between theoretical economics���which presumed buyers and sellers made rational decisions���and real life. I had irrational spending habits and often made bad purchases that I figured I could worry about ���later.���
My classroom textbook explained that a credit card was like a temporary loan from the bank. But I came to realize I was actually borrowing from my future self, with the expectation that the debt would be easily repaid because inflation would make the debt worth less and because I would supposedly have more money. Being a teacher paying off a lawyer���s debt, I saw the folly of it all. Meanwhile, my high school students were reading about how to spend rationally ���when they become consumers in the future,��� only to immediately run to the mall after school.
I began studying behavioral economics, especially the psychology of consumerism, which would become popular 10 years later with the publication of Steven Levitt and Stephen Dubner���s Freakonomics. I became fascinated that consumers, starting as children, get ���nudged��� into irrational spending choices and habits by the media and those around them. I fancied myself a Holden Caulfield of economics, becoming a pioneer in this new field of media literacy. I wrote articles and eventually three textbooks on the subject.
This academic foray helped me to reassess and cut back my own spending. I shopped at discount stores for clothes. I���d make a vat of chili and then eat it for the next week, rather than going to restaurants every night. I was still a tech-loving geek. But I began looking at the features offered by computers and other devices���the ones advertisers said I had to have���and asking if I actually needed the upgrade. Dating became more fun, as I no longer posed as a high roller but could relax and say, ���This is me and where I am. If it works, great. If not, nice to have met you.���
Along with hikes, my son Ben and I had a regular outing for burgers and shakes, during which we rolled out a chessboard and I taught him how to play. One time, I even heard a sigh and looked up to see several single moms smiling and even giving me the once-over.
Meeting Jiab. Redirecting a ship from its nearly 40-year course is tough, and better done with help. I found the right co-captain in January 2002. I���d been using what was then seen as the new ���weird��� system of online dating. I actually liked it because I could look over profiles and decide if a woman might be a good fit. If we had different core values, such as she only wanted men of a particular faith, or didn���t want to be a parent, or wanted a high-end lifestyle, I knew it wouldn���t work.
I won���t get into all the things in Jiab���s profile that attracted me, but there is one facet that sums up our different financial attitudes. I had bought a year���s online dating subscription but would ignore it for a month at a time. I just liked having it there when I needed it. Jiab, by contrast, signed up for the 30-day free trial and wasn���t going to subscribe���read ���pay������after that. I happened to catch her during the trial period. Lucky that I did, because it was magic.
We met for coffee after she had done yoga. So enamored was I that I immediately and impulsively offered to buy her dinner, going back to my old spending habits. Unable to resist a freebie, Jiab accepted. I went home and immediately wrote her an email. I apologized for not playing it cool by waiting a few days to then casually ask if she wanted to get together. I said I didn���t want to risk losing an opportunity with a great woman by playing games. It worked.
I was also lucky that we met after I had started to right my financial ship. If it had been earlier, I don���t think Jiab and I would have jibed. But as things stood, we agreed on our general outlook on money management. We both believed in saving as much as possible and maxing out our retirement accounts. We also���and this is essential���believed in the greater value of experiences, especially varied ones, over the power of owning things.
For example, we did the obligatory family Disney World vacation. Even then, Jiab and I sat through a time-share presentation to get free tickets. If you ask our two children���Jiab also has a son from an earlier marriage���more fun was had on the family trip done on the cheap, where we backpacked through New York, Philadelphia and Washington, D.C., staying in hostels, taking trains, walking and, yes, carrying all our stuff in backpacks.
Jiab and I differ in two ways. First, she���s detail-oriented. She knows every dollar we have, where it is and what it���s doing for us. She has her head down micromanaging to make sure we have the quantity of money necessary for a good life. Jiab has earned a reputation on three continents for her reluctance to spend. Meanwhile, I focus more on the quality of life and advocate for judiciously releasing our grip on funds to get all we can from an experience. For example, having a pet really makes no sense financially, but my joy at having cats got Jiab hooked and we have had a houseful ever since.
I don���t need her to tell me I was right on those occasions. Her smile at enjoying a rare carefree-about-money moment is enough. Some of my old habits are still hard to shake. Sometimes, I don���t bother to look at prices or shop around much when I feel something is a ���necessity,��� like food or a home repair. To this day, when I start to say, ���Just get it,��� Jiab will give me a not-so-subtle hint by asking, ���But how much does it cost? Is there another place we can get it cheaper?��� For us, tipping remains a negotiation.
The other area we differ on is the tradeoff between time and money. Jiab will spend hours looking to save just a few more dollars, but���and I���m sorry, honey���is terrible about wasting time. She���s always surprised at how late the hour is and how behind she gets. I, on the other hand, am stingy about time. I want to ���get ���er done��� and move on to the next thing. It���s a product of managing a classroom for so long, or perhaps my ADHD. Jiab spends time to get money, and I���ll spend money to get time.
The key to us is that we don���t counter, we complement. At the heart of our marriage, and even when we disagree financially, there���s a mutual respect and willingness to reexamine our beliefs and maybe trust the other���s view. We aren���t either-or. Rather, we���re like the yin-yang that���s completed by the other���s viewpoint.
When we take family vacations, Jiab will plot the travel and find the best places to stay, all maximizing savings. Once we get there, I���m in charge of finding that cool attraction, like a weird museum, a great hiking trail or a haunted spot. Our reciprocal respect often comes out in good-natured teasing. Jiab refers to ���Wassernomics��� when I say we ���made��� money because something was cheaper than we anticipated, or when I contend that a videogame the boys and I want to purchase will be made cheaper every time we play it.
Our differing styles influenced how we raised our two sons. Jiab rightly thought that the boys were getting too many gifts for Christmas, so I found Heifer International, through which ���Santa��� delivered two goats, named after the boys, to a remote village in Africa. The only problem: The day after Christmas, the boys excitedly demanded we visit the goats.
When they were older, we had a Salvation Army Christmas, where everyone agreed to only buy gifts at thrift stores and not spend more than $10 per gift. The hit was the mug with a battery-operated fan that kept chocolate milk mixed. If there was a key to instilling an appreciation for saving money with our sons, I would cite two factors. First, we never presented spending less as a sacrifice, but more as a lifestyle choice to avoid consuming so many resources. Second, we were all in it together and enjoyed it as a fun event.
Going places. When the boys went to university, Jiab and I began downsizing. There was no sense in paying a mortgage on empty rooms that were rarely used. We sold our larger suburban home and moved to a nearby townhome. Without fully realizing it, we were also taking small steps toward the retirement door.
The idea of exploring the world, something we���d always loved doing, crept into more of our conversations. We both liked our work, but had become increasingly bothered by the administrative roadblocks and workplace politics. For years, I could just sit and smile through every staff in-service meeting that proclaimed that a rebranded version of something from a dozen years ago would purportedly revolutionize pedagogy. More and more, however, the irritation lingered after the meetings. I more openly proclaimed my skepticism, probably as an unconscious first step toward announcing that I was done.
The moment of clarity is different for everyone. For me, it was a meeting with a TIAA financial advisor. Retirement was one of those ���someday��� states of mind���until the advisor said he ran our savings through a Monte Carlo analysis and determined that the odds our money would be enough for the rest of our lives was over 99%.
Done.
The entire drive home, I kept thinking, ���We did it.��� By the time I got home, however, my thought was, ���We now do��� what?���
We began planning our life���s next phase. True to our roles, I dreamt and read, Jiab crunched. We wanted to travel, but we���d always favored rubbing elbows with locals and living like them. Rather than taking glamorous cruises and vacationing behind resort walls while devouring Americanized versions of local fare, we preferred staying in modest hotels and eating street food. To us, it's a more authentic experience. To our wallets, it���s more cost-effective. We wanted the same experience now, just more extended.
We settled on relocating ourselves to a place from which we could explore the world. Once our boys graduated university, we knew we had a window of time between then, when they wanted to be on their own, and when we might get the call that we were to be grandparents and once again needed.
We first considered Costa Rica. It had great expat reviews, a relatively low cost of living and was only a two-hour flight from the U.S. Soon, however, we were looking farther afield. We discovered that for about the same cost as Costa Rica���$30,000 per year���we could live in southern Spain. That would give us easy access to the rest of Europe.
We looked into Spanish visas and, the next thing we knew, we were in Houston getting them. We chose Granada, in Andalusia, as our initial landing spot, but ended up asking the flat owner if he was willing to make it a year-long lease. Of course, Jiab handled the paperwork. I added color commentary, encouragement, made coffee and looked for Spanish language courses.
Once we reached Spain, there were further hurdles, such as having to set up financial accounts and learning that many aspects of official business seemed stuck in the 1500s, when Spain was the world���s dominant empire. Most everything, from government interactions to banking, was still best done in person and on paper.
For all the annoyances, we only had to take a walk in the mountains, or on the beach, or have tapas and wine followed by a siesta, to remind us that annoyance was the price of choice and privilege. We remained grateful for having both. When not wandering and wondering, we strove for the Hemingway-like writer���s life abroad. The house full of entitled cats was a good start.
Three years later, we returned to the States. We had family matters to attend to. We also missed the boys. COVID isolation brought that point���and us���home. We���re still secure in our savings and enjoying what is the essential power of money, which is the power to choose.
America was founded to give people the right to pursue happiness, but the pursuit is not free. There are charges all along the way. As a young man, my pursuit was prepaid. I didn���t really learn how to play the game until my 1990s wipeout.
Much of my good fortune has stemmed from the luck of the birth lottery and the help of others. But I also helped myself with some good choices and some key adjustments made by my younger self. To that, I keep hearing the words of an old tae kwon do teacher who would���on the rare occasions I adjusted my sparring strategy to take advantage of an opening���drop his scowl, nod and offer his highest praise, ���Not bad, Wasserman.���
Jim Wasserman is a former business litigation attorney who taught economics and humanities for 20 years. He's the author of a three-book series on how to teach elementary, middle and high school students about behavioral economics and media literacy. He's also authored several educational children's books. Jim lives in Texas with his wife and fellow HumbleDollar contributor, Jiab. Together, they're currently working on a book, ���Your Third Life: Reflections on Finding Our Way by Taking the Long Route.��� Check out Jim's earlier��articles.
I grew up with just about every privilege a person could want. My family was as stereotypical a nuclear, suburban, well-to-do group as any seen on a TV sitcom. I never wanted for food, shelter, top-flight schooling or the latest comforts. I was born wealthy, male and white in America. The road to success was flat and freshly paved.
Budgets, paying bills and other pragmatic aspects of finance were discussed in our family. But I kept all this knowledge at arm's length. Money was, for me, a valued but undefined resource that didn���t necessarily need management, like living in a forest and never worrying about running out of timber.

He was also pragmatic. I remember excitedly showing him one of my comic books that was, according to a collector���s guide, worth $50. My father smiled and asked, ���Do you know anyone right now who will pay you $50 for that comic?��� When I sheepishly said no, he put his arm on my shoulder and said, ���Then it���s not worth $50.���
If Pop had a fault, it was that he was too generous with his kids. He wanted us to be free of money worries so we could pursue our dreams. But there was a cost. While I learned to stay mostly within my allowance and spend reasonably, there was no harsh penalty for blowing the budget once in a while. I learned about stocks and watched interest rates���I grew up during the inflationary 1970s���but I also knew I had a safety net if I made a bad choice. My privilege told me that money took care of itself. I needn���t worry about paying for college and law school, so I didn���t.
One good lesson I learned from watching my father���though it didn���t immediately stick���was that just because we could afford the best didn���t mean we should spend that much. If a salesman tried to talk my father into buying the high-end deluxe model, my father would point-blank ask, ���Tell me what exactly makes this version worth so much more than the other one, and then I���ll judge.��� We learned that the basic version of things, like a car, was almost always enough.
I came out of law school ready to take on the world and, with a good job in hand, I again didn���t need to worry about money. I had plenty to live on and even invest. I bought stocks and municipal bonds. I won���t say I bought wisely. It was pretty much hunches supported by a little research. Despite being mid-20s and having spent almost all my life in school, I thought of myself as an advanced investor because I was using the latest high tech, in the form of a 640 KB RAM personal computer, as well as programs like Quicken, to monitor it all. In truth, I was like a novice driver in a Ferrari.
When spending, I resisted buying big-ticket items, except, of course, those that I ���needed,��� like expensive designer suits to play power litigator in court. Where I was most undisciplined was day-to-day expenses. I usually ate at good restaurants. If I needed something, I opted for convenience, rather than spending time shopping for a better deal. Also, at this point, in my haughty 20-something-knows-everything mind, I opted to counter my father���s example and buy more expensive versions of everything from tires to furniture to wine. That way, in my na��ve thinking, I knew I was getting quality.
I married another lawyer and we moved to Dallas, each working for a different law firm. We bought a starter home and began a family with the birth of our son. We each saved and invested, but we kept our investments mostly separate, except for shared things like the mortgage.
My rude awakening. For the U.S., the 1990s was a time of strong growth. For me, it was my crash. I came to realize what I had felt intuitively for a long time: I hated being a lawyer. It was what society said was ���success,��� but it wasn���t for me. I was raised with a sense of noblesse oblige, that my privilege not only allowed��me to give back to society, but that I had a duty to do so. As a business litigation attorney, I was giving little back, instead simply moving piles of money from one rich party to another, while also keeping a chunk for the law firm. I hated the monotonous day-to-day grind. It showed in my work and attitude. I was paid well, but I put on weight and had chest pains.
I quit law. Lawyers don���t have a lot of transferable skills���that���s why they���re usually the first chosen to be eaten in surveys of people told to imagine they were marooned. I looked around for what I could do to both serve humanity and still serve my son food. I found it in teaching. I put together a resume and sent off letters to schools, saying I was a lawyer who wanted to teach and please give me a shot. I substitute-taught to see if I liked it and could handle being in a classroom. I loved it.
During this time, I had a long lunch with my father, discussing my career transition. He just wanted me to be happy. For my part, I told him I owed him an apology. Growing up among elite kids, I was somewhat embarrassed that my father was so bourgeois as to make money by manufacturing curtains and bedspreads. I now realized that he made a tangible product that improved people���s lives and, in the process, he and Mom created a wonderful environment for their kids to grow up in. I���m glad I got to say this before his passing.
At around the same time, my marriage fell apart. My now ex-wife and I were friends who had the law in common, but we weren���t good as a couple. For one, I had already lived with privilege, and didn���t really desire club memberships and the latest doo-dads. Been there, done that. My ex had grown up modestly in a rural town where young girls were told the best they could do was marry the local seed salesman. Law and the lawyer lifestyle were her vehicles to self-reliance and to prove her worth.
Neither of us was right or wrong, but we had different aspirations. Now that I wasn���t a lawyer and could no longer afford to spend without thought, the marriage crumbled. She retained primary custody of our son, so she got the lion���s share of our assets. I put most of the assets I had to give her into a college fund for our son.
Luckily, I proved good at teaching and managed to get a great job and remain employed for the rest of my career. The problem: I was pretty much starting over. My savings were gone in the divorce. I had the spending habits of a lawyer, but a teacher���s salary. I was forced to limit how often I ate out and care whether something was on sale. I had one fancy leftover bit of bling, a shiny red convertible with a $450 monthly lease payment. I broke the lease, paid a large penalty and bought a plain PT Cruiser. My toddler son was disappointed that we could no longer jump in and out of the convertible, but he loved the Chrysler emblem on the Cruiser because it looked like Harry Potter���s golden snitch. It was a reminder that it isn���t things that bring meaning to our lives. Rather, it���s the meaning and appreciation we invest in them.
I tried to live within a budget, but having never done so, it took a long time to corral my spending. Still, I maxed out my contributions to my 403(b) plan. Our school���s retirement services manager, TIAA-CREF, made it easy to do basic research and pick funds. I was finally able to join the rest of the country���s rising 1990s portfolios by buying global funds, tech shares and some adventurous gambles on small-cap funds.
Even as I invested, though, the credit card was my best friend and worst enemy. I had, of course, endless offers for new cards, with assurances I only had to pay the minimum each month. I never bought big, but the ���what the heck��� instances were like body blows to my credit score.
I had two weaknesses. First, I tried to keep up with my ex. If she took my son on a great vacation or bought him tons of gifts, I feared he would prefer her, so I acted like a third-world economy trying to keep pace with a first-world one. Eventually, I had to look for shortcuts and freebies. Instead of vacations, we did ���buddy hikes��� and made secret buddy caves in the woods. We saved cardboard, and built forts and other things.
My other big money leak was dating. I was fixed up with lawyers, businesswomen and other professionals. The expectation was to ���do the town.��� Flowing cash would supposedly make the evening flow better. I was even told by a dating consultant to lie and say I was still a lawyer because ���no woman wants to date a teacher.���
Ironically, while I was watching my debt rise, I began teaching economics and started seeing a disconnect between theoretical economics���which presumed buyers and sellers made rational decisions���and real life. I had irrational spending habits and often made bad purchases that I figured I could worry about ���later.���
My classroom textbook explained that a credit card was like a temporary loan from the bank. But I came to realize I was actually borrowing from my future self, with the expectation that the debt would be easily repaid because inflation would make the debt worth less and because I would supposedly have more money. Being a teacher paying off a lawyer���s debt, I saw the folly of it all. Meanwhile, my high school students were reading about how to spend rationally ���when they become consumers in the future,��� only to immediately run to the mall after school.
I began studying behavioral economics, especially the psychology of consumerism, which would become popular 10 years later with the publication of Steven Levitt and Stephen Dubner���s Freakonomics. I became fascinated that consumers, starting as children, get ���nudged��� into irrational spending choices and habits by the media and those around them. I fancied myself a Holden Caulfield of economics, becoming a pioneer in this new field of media literacy. I wrote articles and eventually three textbooks on the subject.
This academic foray helped me to reassess and cut back my own spending. I shopped at discount stores for clothes. I���d make a vat of chili and then eat it for the next week, rather than going to restaurants every night. I was still a tech-loving geek. But I began looking at the features offered by computers and other devices���the ones advertisers said I had to have���and asking if I actually needed the upgrade. Dating became more fun, as I no longer posed as a high roller but could relax and say, ���This is me and where I am. If it works, great. If not, nice to have met you.���
Along with hikes, my son Ben and I had a regular outing for burgers and shakes, during which we rolled out a chessboard and I taught him how to play. One time, I even heard a sigh and looked up to see several single moms smiling and even giving me the once-over.
Meeting Jiab. Redirecting a ship from its nearly 40-year course is tough, and better done with help. I found the right co-captain in January 2002. I���d been using what was then seen as the new ���weird��� system of online dating. I actually liked it because I could look over profiles and decide if a woman might be a good fit. If we had different core values, such as she only wanted men of a particular faith, or didn���t want to be a parent, or wanted a high-end lifestyle, I knew it wouldn���t work.
I won���t get into all the things in Jiab���s profile that attracted me, but there is one facet that sums up our different financial attitudes. I had bought a year���s online dating subscription but would ignore it for a month at a time. I just liked having it there when I needed it. Jiab, by contrast, signed up for the 30-day free trial and wasn���t going to subscribe���read ���pay������after that. I happened to catch her during the trial period. Lucky that I did, because it was magic.
We met for coffee after she had done yoga. So enamored was I that I immediately and impulsively offered to buy her dinner, going back to my old spending habits. Unable to resist a freebie, Jiab accepted. I went home and immediately wrote her an email. I apologized for not playing it cool by waiting a few days to then casually ask if she wanted to get together. I said I didn���t want to risk losing an opportunity with a great woman by playing games. It worked.
I was also lucky that we met after I had started to right my financial ship. If it had been earlier, I don���t think Jiab and I would have jibed. But as things stood, we agreed on our general outlook on money management. We both believed in saving as much as possible and maxing out our retirement accounts. We also���and this is essential���believed in the greater value of experiences, especially varied ones, over the power of owning things.
For example, we did the obligatory family Disney World vacation. Even then, Jiab and I sat through a time-share presentation to get free tickets. If you ask our two children���Jiab also has a son from an earlier marriage���more fun was had on the family trip done on the cheap, where we backpacked through New York, Philadelphia and Washington, D.C., staying in hostels, taking trains, walking and, yes, carrying all our stuff in backpacks.
Jiab and I differ in two ways. First, she���s detail-oriented. She knows every dollar we have, where it is and what it���s doing for us. She has her head down micromanaging to make sure we have the quantity of money necessary for a good life. Jiab has earned a reputation on three continents for her reluctance to spend. Meanwhile, I focus more on the quality of life and advocate for judiciously releasing our grip on funds to get all we can from an experience. For example, having a pet really makes no sense financially, but my joy at having cats got Jiab hooked and we have had a houseful ever since.
I don���t need her to tell me I was right on those occasions. Her smile at enjoying a rare carefree-about-money moment is enough. Some of my old habits are still hard to shake. Sometimes, I don���t bother to look at prices or shop around much when I feel something is a ���necessity,��� like food or a home repair. To this day, when I start to say, ���Just get it,��� Jiab will give me a not-so-subtle hint by asking, ���But how much does it cost? Is there another place we can get it cheaper?��� For us, tipping remains a negotiation.
The other area we differ on is the tradeoff between time and money. Jiab will spend hours looking to save just a few more dollars, but���and I���m sorry, honey���is terrible about wasting time. She���s always surprised at how late the hour is and how behind she gets. I, on the other hand, am stingy about time. I want to ���get ���er done��� and move on to the next thing. It���s a product of managing a classroom for so long, or perhaps my ADHD. Jiab spends time to get money, and I���ll spend money to get time.
The key to us is that we don���t counter, we complement. At the heart of our marriage, and even when we disagree financially, there���s a mutual respect and willingness to reexamine our beliefs and maybe trust the other���s view. We aren���t either-or. Rather, we���re like the yin-yang that���s completed by the other���s viewpoint.
When we take family vacations, Jiab will plot the travel and find the best places to stay, all maximizing savings. Once we get there, I���m in charge of finding that cool attraction, like a weird museum, a great hiking trail or a haunted spot. Our reciprocal respect often comes out in good-natured teasing. Jiab refers to ���Wassernomics��� when I say we ���made��� money because something was cheaper than we anticipated, or when I contend that a videogame the boys and I want to purchase will be made cheaper every time we play it.
Our differing styles influenced how we raised our two sons. Jiab rightly thought that the boys were getting too many gifts for Christmas, so I found Heifer International, through which ���Santa��� delivered two goats, named after the boys, to a remote village in Africa. The only problem: The day after Christmas, the boys excitedly demanded we visit the goats.
When they were older, we had a Salvation Army Christmas, where everyone agreed to only buy gifts at thrift stores and not spend more than $10 per gift. The hit was the mug with a battery-operated fan that kept chocolate milk mixed. If there was a key to instilling an appreciation for saving money with our sons, I would cite two factors. First, we never presented spending less as a sacrifice, but more as a lifestyle choice to avoid consuming so many resources. Second, we were all in it together and enjoyed it as a fun event.
Going places. When the boys went to university, Jiab and I began downsizing. There was no sense in paying a mortgage on empty rooms that were rarely used. We sold our larger suburban home and moved to a nearby townhome. Without fully realizing it, we were also taking small steps toward the retirement door.
The idea of exploring the world, something we���d always loved doing, crept into more of our conversations. We both liked our work, but had become increasingly bothered by the administrative roadblocks and workplace politics. For years, I could just sit and smile through every staff in-service meeting that proclaimed that a rebranded version of something from a dozen years ago would purportedly revolutionize pedagogy. More and more, however, the irritation lingered after the meetings. I more openly proclaimed my skepticism, probably as an unconscious first step toward announcing that I was done.
The moment of clarity is different for everyone. For me, it was a meeting with a TIAA financial advisor. Retirement was one of those ���someday��� states of mind���until the advisor said he ran our savings through a Monte Carlo analysis and determined that the odds our money would be enough for the rest of our lives was over 99%.
Done.
The entire drive home, I kept thinking, ���We did it.��� By the time I got home, however, my thought was, ���We now do��� what?���
We began planning our life���s next phase. True to our roles, I dreamt and read, Jiab crunched. We wanted to travel, but we���d always favored rubbing elbows with locals and living like them. Rather than taking glamorous cruises and vacationing behind resort walls while devouring Americanized versions of local fare, we preferred staying in modest hotels and eating street food. To us, it's a more authentic experience. To our wallets, it���s more cost-effective. We wanted the same experience now, just more extended.
We settled on relocating ourselves to a place from which we could explore the world. Once our boys graduated university, we knew we had a window of time between then, when they wanted to be on their own, and when we might get the call that we were to be grandparents and once again needed.
We first considered Costa Rica. It had great expat reviews, a relatively low cost of living and was only a two-hour flight from the U.S. Soon, however, we were looking farther afield. We discovered that for about the same cost as Costa Rica���$30,000 per year���we could live in southern Spain. That would give us easy access to the rest of Europe.
We looked into Spanish visas and, the next thing we knew, we were in Houston getting them. We chose Granada, in Andalusia, as our initial landing spot, but ended up asking the flat owner if he was willing to make it a year-long lease. Of course, Jiab handled the paperwork. I added color commentary, encouragement, made coffee and looked for Spanish language courses.
Once we reached Spain, there were further hurdles, such as having to set up financial accounts and learning that many aspects of official business seemed stuck in the 1500s, when Spain was the world���s dominant empire. Most everything, from government interactions to banking, was still best done in person and on paper.
For all the annoyances, we only had to take a walk in the mountains, or on the beach, or have tapas and wine followed by a siesta, to remind us that annoyance was the price of choice and privilege. We remained grateful for having both. When not wandering and wondering, we strove for the Hemingway-like writer���s life abroad. The house full of entitled cats was a good start.
Three years later, we returned to the States. We had family matters to attend to. We also missed the boys. COVID isolation brought that point���and us���home. We���re still secure in our savings and enjoying what is the essential power of money, which is the power to choose.
America was founded to give people the right to pursue happiness, but the pursuit is not free. There are charges all along the way. As a young man, my pursuit was prepaid. I didn���t really learn how to play the game until my 1990s wipeout.
Much of my good fortune has stemmed from the luck of the birth lottery and the help of others. But I also helped myself with some good choices and some key adjustments made by my younger self. To that, I keep hearing the words of an old tae kwon do teacher who would���on the rare occasions I adjusted my sparring strategy to take advantage of an opening���drop his scowl, nod and offer his highest praise, ���Not bad, Wasserman.���

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Published on June 03, 2022 22:00
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